Acetic Acid → HCID 19804848, compound

HRID 1682181Notes

Reaction equation

HRID 1682181 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13]C(C#N)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:18]([OH:21])(=[O:20])[CH3:19]>>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:19]([C:18]([OH:21])=[O:20])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 467807704-(Benzyloxy)cyclohexane-1-carbonitrile

Product 1

HCID 19804848HCID 19804848, compound

Procedure

The crude 4-benzyloxycyclohexane-1-nitrile (4.0 g) was refluxed with stirring with a mixture of glacial acetic acid (16 ml) and concentrated hydrochloric acid (24 ml) for 20 hours. The reaction mixture was cooled, the solid removed by filtration and washed with water. The product was ground with 2M sodium hydroxide solution (70 ml) and then diluted with water. Unchanged nitrile was removed by filtration and the filtrate acidified with concentrated hydrochloric acid. White crystals separated and were collected by filtration, washed with water and dried to yield 4-benzyloxycyclohexane-1-carboxylic acid m.p. 170°-180° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solid removed by filtration
  3. washwashed with water
  4. additiondiluted with water
  5. customUnchanged nitrile was removed by filtration
  6. customWhite crystals separated
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-08d2b09397964fa7a6e3c2fc71fbb982
Source dataset
uspto-grants-1992_12
Patent number
US05175319

Reaction notes

Loading…